Ionic liquid based support for manufacture of peptides

Patent metadata

Field	Value
Publication number	US-2020140480-A1
Application number	US-201716473381-A
Country	US
Kind code	A1
Filing date	Dec 28, 2017
Priority date	Dec 28, 2016
Publication date	May 7, 2020
Grant date	—

Abstract

The present invention relates to an ionic liquid based support of Formula-I: wherein: X − is a heteroatom containing cationic part; W is a halogen containing polymeric solid support; n is an integer in the range of 2 to 8; Y is a hydrophobic anion; R is selected from CO—Z or Z; Z is selected from the group consisting of —Cl, —Br, —OH, —O-Alkyl and combinations thereof. The present invention also relates to a process for preparation of said ionic liquid based support used for di, oligo or polypeptide manufacture.

First claim

We claim:

1 . An ionic liquid based support of Formula-I:

wherein: X + is a heteroatom containing cationic part;
W is a halogen containing polymeric solid support;
n is an integer in the range of 2 to 8;
Y − is a hydrophobic anion;
R is selected from CO—Z or Z;
Z is selected from the group consisting of —Cl, —Br, —OH, —O-Alkyl and combinations thereof.

2 . The ionic liquid based support as claimed in claim 1 , wherein R is CO—Z.

3 . The ionic liquid based support as claimed in claim 1 , wherein R is Z.

4 . The ionic liquid based support as claimed in claim 1 , wherein the ionic liquid based support has a mesh size in the range of 10 to 70.

5 . The ionic liquid based support as claimed in claim 1 , wherein the heteroatom containing cationic part is selected from the group consisting of imidazole, triethylamine, diethanolamine, diethyl amine, pyridine, triethanolamine, triethylphosphine and combinations thereof.

6 . The ionic liquid based support as claimed in claim 1 , wherein the halogen containing polymeric solid support is selected from the group consisting of chloromethyl polystyrene, hydroxyethylpolystyrene, divinyl benzene crosslinked chloromethyl polystyrene and combinations thereof.

7 . The ionic liquid based support as claimed in claim 1 , wherein the hydrophobic anion is selected from the group consisting of methane sulfonate, triflate, hexafluorophosphate, trifluoromethanesulfonate, bistrifluoromethane sulfanimide, tetrafluroborate and combinations thereof.

8 . The ionic liquid based support as claimed in claim 1 , wherein the ionic liquid based support further comprises of ionic solvent.

9 . The ionic liquid based support as claimed in claim 7 , wherein the ionic solvent is selected from the group consisting of triethylamine, diethanolamine, triethanolamine, diethyl amine, imidazole, triethylphosphine based functionalized ionic liquid.

10 . A method for the preparation of an ionic liquid based support, comprising:
i) attaching a heteroatom containing cationic part (X + ) of an ionic liquid with a halogen containing polymeric solid support in an organic solvent at temperature in the range of 40° C. to 110° C. to obtain a solid product; ii) washing the solid product with another organic solvent to obtain a washed solid product; iii) subjecting the washed solid product to anion metathesis using a less hydrophilic or hydrophobic anionic source selected from the group consisting of methane sulfonate, triflate, hexafluorophosphate, trifluoromethanesulfonate, bistrifluoromethane sulfanimide, and tetrafluroborate or combinations thereof in a solvent under stirring conditions at a temperature ranging from 20° C. to 60° C. obtain an anion metathesis product; iv) drying the metathesis product at a temperature ranging from 60° C. to 120° C. under reduced pressure in between 60 mm Hg to 20 mm of Hg to obtain ionic liquid based support.

11 . The method as claimed in claim 9 , wherein the organic solvent is selected from a group of toluene, acetonitrile, ethanol, and acetone or combinations thereof.

12 . The method as claimed in claim 9 , wherein the solid product is washed with another organic solvent selected from the group consisting of diethyl ether, acetone, ethanol, and toluene or combinations thereof.

13 . The method as claimed in claim 9 , wherein the solvent is selected from the group consisting of dichloromethane, water, ethanol and combinations thereof.

Assignees

• Indian Institute Tech Delhi

Inventors

• Upadhyayula Sreedevi
• Patra Tanmoy
• Paul Subhasis

Classifications

• C08F8/32

  by reaction with amines · CPC title

• C07K1/042 Primary

  characterised by the nature of the carrier · CPC title

• C08F12/18

  Chlorine · CPC title